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通过四氯化锆催化的三组分反应合成5-氨基和5-亚氨基咪唑并[1,2 -]咪唑的新型高效方法的开发。

Development of Novel and Efficient Processes for the Synthesis of 5-Amino and 5-Iminoimidazo[1,2-]imidazoles via Three-Component Reaction Catalyzed by Zirconium(IV) Chloride.

作者信息

Driowya Mohsine, Guillot Régis, Bonnet Pascal, Guillaumet Gérald

机构信息

Institut de Chimie Organique et Analytique, Université d'Orléans, UMR CNRS 7311, Orléans, France.

Institut de Chimie Moléculaire et des Matériaux d'Orsay, Université Paris Sud, Université Paris Saclay, UMR CNRS 8182, Orsay, France.

出版信息

Front Chem. 2019 Jul 8;7:457. doi: 10.3389/fchem.2019.00457. eCollection 2019.

DOI:10.3389/fchem.2019.00457
PMID:31338360
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6628877/
Abstract

General and efficient approaches for the synthesis of new 5-amino and 5-iminoimidazo[1,2-]imidazoles were developed through a three-component reaction of 1-unsubstituted 2-aminoimidazoles with various aldehydes and isocyanides mediated by zirconium(IV) chloride. The protocols were established considering the reactivity of the starting substrate, which varies depending on the presence of a substituent on the 2-aminoimidazole moiety. A library of new N-fused ring systems with wide structural diversification, novel synthetic, and potential pharmacological interest was obtained in moderate to good yields.

摘要

通过1-未取代的2-氨基咪唑与各种醛和异氰化物在四氯化锆介导下的三组分反应,开发了合成新型5-氨基和5-亚氨基咪唑并[1,2 -]咪唑的通用且高效的方法。考虑到起始底物的反应性建立了该方案,其反应性根据2-氨基咪唑部分上取代基的存在而变化。获得了一系列具有广泛结构多样性、新颖合成方法和潜在药理学意义的新型N-稠环体系,产率适中至良好。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ac5/6628877/a97c60b2a305/fchem-07-00457-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ac5/6628877/a97c60b2a305/fchem-07-00457-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4ac5/6628877/a97c60b2a305/fchem-07-00457-g0001.jpg

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